Family-friendly holiday rentals in Bridgewater

4.93 out of 5 average rating, 348 reviews

A round yurt is surrounded by lush green trees, with a tan conical roof and large windows that invite natural light. The pathway leading to the entrance is bordered by various plants and shrubs, enhancing the connection to the natural setting.

Yurt in Bristol

Bristol Cozy Yurt near Hiking/Skiing|MapleFarm

Our cozy yurt is located within minutes of amazing, hiking, biking, skiing, breweries and much more! Relax around the fire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking and swimming skiing in Central Vermont. Mt Abe and Bartlett's Falls are the closest options. We're also close to civilization with several towns close by to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

4.99 out of 5 average rating, 152 reviews

A yurt with a beige and red exterior is surrounded by lush greenery. A wooden deck leads to the entrance, with comfortable seating visible. The backdrop features trees and an open view of the hillside, illuminated by natural light under a clear blue sky.

Yurt in Randolph

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

4.97 out of 5 average rating, 244 reviews

A spacious living area features a corner sectional sofa adorned with a cozy blanket and accented by a wooden wall with decorative planters. A rustic coffee table sits in front of the sofa, while a gas fireplace stove provides warmth and ambiance.

Cottage in Bridgewater

Newly Renovated, Hot tub, 2min to Killington lift

Stone’s Throw Vermont is a 3 bed/1.5 bath cottage with hot tub, fireplace, and space for 6 guests conveniently located in central Vermont. Placed right on the US-4 corridor; you’re 2 minutes from the Killington Ski Resort’s Skyship Ski Gondola escorting you to the world class amenities of Killington Resort, 5 min from the best craft beer in the region at Long Trail Brewery, 10 min to Echo Lake, and 20 min from the shops and cafes of Woodstock, VT. Truly everything is a Stone’s Throw away.

4.92 out of 5 average rating, 109 reviews

A red cabin with a metal roof is framed by tall yellow wildflowers and lush greenery. The spacious porch features white railing and is decorated with several seating areas, offering a serene view of the surrounding landscape.

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.94 out of 5 average rating, 312 reviews

A modern cabin is situated among trees, surrounded by greenery. Two Adirondack chairs are positioned near a fire pit, which has gentle smoke rising. A picnic table rests nearby, providing a comfortable outdoor gathering space with views of the natural landscape.

Tiny home in Hartland

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

4.99 out of 5 average rating, 698 reviews

A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

4.97 out of 5 average rating, 421 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

5 out of 5 average rating, 281 reviews

The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

4.98 out of 5 average rating, 274 reviews

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guest house in Woodstock

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.96 out of 5 average rating, 152 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

4.96 out of 5 average rating, 127 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.

4.98 out of 5 average rating, 135 reviews

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

Popular amenities for Bridgewater family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.87 out of 5 average rating, 142 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

4.96 out of 5 average rating, 539 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

Cozy Bow House Perched in Trees w/ Hot Tub & View

4.94 out of 5 average rating, 339 reviews

A modern wood stove stands prominently, emitting a warm glow from the flames inside. A stylish armchair is positioned nearby, with a woven basket beside it. A pair of hiking boots rests lightly on the floor, complementing the cozy atmosphere of the space.

Cabin in Royalton

Scandinavian design Cabin w/ private hiking trail

4.94 out of 5 average rating, 453 reviews

A custom-made yurt is nestled among lush greenery, surrounded by tall trees. Sunlight filters through the foliage, illuminating the yurt's circular structure and chimney. Wildflowers and grasses frame the foreground, creating a natural, serene setting.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

4.9 out of 5 average rating, 247 reviews

A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.

Tiny home in Clarendon

Secluded tiny house resort - DOG FRIENDLY

Guest suite in Brownsville

A recently renovated property is set against a backdrop of lush greenery, featuring a well-maintained lawn and blooming flower beds. The exterior showcases a gray siding, with several large windows allowing natural light into the inviting interior.

4.89 out of 5 average rating, 141 reviews

Newly renovated private space on Ascutney Trails

4.86 out of 5 average rating, 113 reviews

A blue house is nestled among vibrant autumn foliage. A directional sign labeled 'Skyeship House' points the way along a gravel path leading towards the front entrance, framed by trees showcasing warm seasonal colors.

Flat in Bridgewater

Killington Skyeship 4 BR | 1 Min Gondola + Hot Tub

4.92 out of 5 average rating, 509 reviews

A peaceful scene is depicted, showcasing vibrant autumn foliage reflected in the calm waters of a small pond. The rustic cabin is nestled among the trees in the background, complemented by a canoe resting at the water's edge.

Cabin in Bethel

Rustic and Cozy Vermont Getaway at Sugarwood Cabin

Family- and pet-friendly home rentals

4.79 out of 5 average rating, 112 reviews

An A-Frame chalet is partially covered in snow, surrounded by a winter landscape. Snowmobiles are parked in front, with a vehicle also snow-blanketed. The wooden balcony and large windows suggest a cozy interior, while the sloped roof reflects the seasonal setting.

Chalet in Stockbridge

"Swiss Charm"- A Beautiful Riverfront Chalet

4.91 out of 5 average rating, 948 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guest house in Granville

Moon Valley Country Retreat no clean fee pets yes

4.85 out of 5 average rating, 175 reviews

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

Chalet in Stockbridge

Vermont Chalet

Earthen home in Granville

The interior of a cozy yurt features an orange clay wall and a wooden ceiling with exposed beams. A spacious bed is dressed in white linens, and a small desk with a chair sits nearby. A wood stove is positioned next to a area rug, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 147 reviews

Earthen Yurt in Green Mtn Wonderland

4.84 out of 5 average rating, 104 reviews

The exterior of a contemporary timber home is visible, featuring a sloped green metal roof and warm wood siding. Surrounding snow-covered ground reflects nearby evergreen trees. The property is situated on a spacious lot, offering a serene winter landscape.

Townhouse in Killington

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC

Guest suite in Lake Bomoseen

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

4.97 out of 5 average rating, 232 reviews

My house is your house!

4.91 out of 5 average rating, 412 reviews

The outdoor view showcases a house illuminated with colorful holiday lights against a backdrop of dark, snowy terrain. A covered porch is visible, adding charm to the property. Snow blankets the ground, and evergreen trees frame the scene, enhancing the winter ambiance.

Guest suite in Hartford

Sunny Side Airbnb (dog friendly)

4.93 out of 5 average rating, 334 reviews

The exterior of a renovated private studio apartment is visible, featuring a white house with a green metal roof. A well-maintained lawn surrounds the home, with flowering plants in large pots positioned by the windows. A white mailbox stands near the front of the property.

Flat in Tunbridge

Fairview

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 226 reviews

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

Luxury Condo Tucked in the Heart of Killington

A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.

4.92 out of 5 average rating, 179 reviews

Renovated unit, prime location! Shuttle on/Ski off

4.96 out of 5 average rating, 152 reviews

An open-concept living area showcases rustic wooden beams and large windows, allowing natural light to fill the space. A dining table with wooden chairs is positioned near the kitchen, which features modern appliances and a cozy wood stove on a stone base.

Home in Granville

Epic Views of the Green Mountains

4.88 out of 5 average rating, 262 reviews

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

4.93 out of 5 average rating, 201 reviews

Newly renovated ski retreat at Killington

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

4.78 out of 5 average rating, 310 reviews

Serene Top Floor Condo (resort style amenities)

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.